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Dimethylacetamide → 6-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile

HRID 522257
ノート
印刷プレビュー

反応式

HRID 522257 の反応式
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C[C:23]([N:25](C)C)=O.Cl[C:29]1[N:37]=[C:36]2[C:32]([N:33]=[CH:34][N:35]2[CH3:38])=[C:31]([C:39]2[CH:44]=[CH:43][C:42]([O:45]CC3C=CC(OC)=CC=3)=[C:41]([C:55]([F:58])([F:57])[F:56])[CH:40]=2)[N:30]=1>[Zn].[C-]#N.[Zn+2].[C-]#N.FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O.O>[OH:45][C:42]1[CH:43]=[CH:44][C:39]([C:31]2[N:30]=[C:29]([C:23]#[N:25])[N:37]=[C:36]3[C:32]=2[N:33]=[CH:34][N:35]3[CH3:38])=[CH:40][C:41]=1[C:55]([F:56])([F:57])[F:58]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 31374DimethylacetamideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 1178996942-chloro-6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine

生成物 1

HCID 1370152256-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 23994
Zinc
触媒
HCID 2733347Palladium(II) trifluoroacetate触媒
HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

Zinc (64 mg), 2-(di-tert-butylphosphino)biphenyl (163 mg), zinc cyanide (230 mg), and palladium (II) trifluoroacetate (81 mg) were added to a DMAc (16.5 mL) solution of 2-chloro-6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine (1.1 g) at room temperature in an argon atmosphere, and the mixture was stirred at 100° C. for 3 hours. After the reaction mixture was cooled to room temperature, water was added thereto, then extraction thereof was performed using EtOAc, and the extract was washed with water. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=1:1 to 1:4), whereby a mixture of 6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine-2-carbonitrile and 6-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile (502 mg) was obtained.

後処理

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionextraction
  3. washthe extract was washed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=1:1 to 1:4), whereby
  8. additiona mixture of 6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine-2-carbonitrile

出典と根拠

ORDレコード
ord-9ae48241993d4c53bf1f34d515d62172
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09328118B2

反応ノート

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